Organic peracids

Sahcylaldehyde is readily oxidized, however, to sahcyhc acid by reaction with solutions of potassium permanganate, or aqueous silver oxide suspension. 4-Hydroxybenzaldehyde can be oxidized to 4-hydroxybenzoic acid with aqueous silver nitrate (44). Organic peracids, in basic organic solvents, can also be used for these transformations into benzoic acids (45). Another type of oxidation is the reaction of sahcylaldehyde with alkaline potassium persulfate, which yields 2,5-dihydroxybenzaldehyde (46). 

Peracid Classification. Peracids can be broadly classified into organic and inorganic peracids, based on standard nomenclature. The limited number of inorganic peracids has required no subclassification scheme (4). However, the tremendous number of new organic peracids developed (85) has resulted in proposals for classification. Eor example, a classification scheme based on Hquid chromatography retention times and critical miceUization constants (CMC) of the parent acids has been proposed (89). The parent acids are used because of the instabiHty of the peracids under chromatographic and miceUization measurement conditions. This classification scheme is shown in Table 1. 

Two sohd organic peracids have been utilized ia textile bleaching products. Diperoxydodecanedioic acid, (16), [66280-55-5] a hydrotropic peracid, and the magnesium salt [78948-87-5] of monoperoxyphthaUc acid, (17), [2311-91-3] a hydrophilic peracid, were contained in bleaching products for a short period of time (142). 

Organic Peracids, Their Preparation, Properties, Reactions and Uses, Technical bulletin, PMC Corporation Inorganic Chemicals Division, New York, 1964. 

Enol ethers are readily attacked in buffered medium by electrophilic reagents such as halogens, A -haloamides, perchloryl fluoride and organic peracids to give a-substituted ketones. Similarly, electrophilic attack on... 

The nitrate group is stable to the dilute alkaline conditions required for saponification of secondary acetates although it is cleaved during Wolff-Kishner reduction.Nitrates are stable to chromic acid oxidation in acetic acid, to organic peracids, and to lead tetraacetate.This group is readily split by reduction with zinc in acetic acid. 

Tiiazine A-oxides can be obtained by two general methods by direct oxidation of the parent 1,2,4-tiiazines with organic peracids, and by the formation of the A-oxide group of the 1,2,4-triazine ring by cyclization involving nitro, nitroso (isonitroso), or hydroxylamino groups. 

The oxidizing agent (organic peracid) usually attacks the sulfur from the less hindered side of the substrate to produce the less hindered oxidation product as a major isomer139. 

The oxidizing agent (organic peracid) usually attacks the sulfur from the less hindered side of the substrate to produce the less hindered oxidation product as a major isomer Thus, the observed stereoselectivity means the exclusive formation of the rmti-isomer (a). This conclusion was confirmed by NMR analysis (see Section III.B.4.b) and, clearly, can be extended and generalized with respect to larger cyclic sulfoxide systems. 

Following the isolation of the parent thiirane oxide 16a by the oxidation of thiirane with either sodium metaperiodate or with the t-Bu0H-H20-V205 system, a systematic study was undertakento establish a reliable and general method for the oxidation of thiiranes to thiirane oxides. lodosobenzene, -butyl hypochlorite, N2O4, HjOj and organic peracids have been examined. 

Alkylsulfonic acids are active oxidative agents like other organic peracids. Several oxidative reactions of seodecylsulfonic peracid were studied by Safiullin et al. [41]. Peracid was found to oxidize benzene to phenol as the first intermediate product. The formed sulfonic acid accelerates the reaction. Oxidation occurs according to the stoichiometric equation... 

As stated above, one of the alternatives to using organic peracids for the oxidation of alkenes is the use of hydroperoxides72. Since the latter are practically inert to double... 

The organic peracids like per carboxylic acids are important reagents because they are used to ... 

Epoxidation of olefinic double bonds by organic peracids is a well known reaction whose scope, reliability and usefulness in organic synthesis was established largely by the work of Swem [1], who was also the first to show that the reaction is stereospecific. 

Organic peracids are the most reliable and commonly used oxidizing reagents for various purposes in organic chemistry. Compared to common percarboxylic acids such as performic acid, peracetic acid, perbenzoic acid and m-chloroperbenzoic acid, the first sulfur peroxy acid, i.e. monopersulfuric acid , was reported earlier, already in 1891. 

The oxidation of both aliphatic and aromatic azo compounds to the corresponding azoxy derivative may be carried out with a variety of reagents. While older techniques favored chromic or nitric acid as the oxidizing agent, newer methods make use of various organic peracids or hydrogen peroxide. In the oxidation of aliphatic azo compounds, relatively weak peracids are favored to reduce the possibility of acid-catalyzed isomerization of azo compounds to hydrazones. Under controlled conditions cis azo compounds may be converted into cis azoxy compounds. 

Direct Oxidation with Stoichiometric Oxidants. Discovered by Prilezhaev in 1909,211 the typical epoxidation reaction of alkenes is their oxidation with organic peracids. Of the large number of different peroxycarboxylic acids used in... 

---